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US7022656B2 - Water-soluble copolymer film packet - Google Patents

Water-soluble copolymer film packet Download PDF

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Publication number
US7022656B2
US7022656B2 US10/392,030 US39203003A US7022656B2 US 7022656 B2 US7022656 B2 US 7022656B2 US 39203003 A US39203003 A US 39203003A US 7022656 B2 US7022656 B2 US 7022656B2
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Prior art keywords
copolymer
water
film
soluble
range
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US20040186034A1 (en
Inventor
Andrew P. Verrall
P. Scott Bening
Karen A. Kugler
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Sekisui Specialty Chemicals America LLC
Monosol LLC
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Monosol LLC
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Priority to US10/392,030 priority Critical patent/US7022656B2/en
Application filed by Monosol LLC filed Critical Monosol LLC
Assigned to MONOSOL, LLC reassignment MONOSOL, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BENING, P. SCOTT, KUGLER, KAREN A., VERRALL, ANDREW P.
Priority to US10/723,647 priority patent/US6787512B1/en
Priority to JP2006507299A priority patent/JP2006521449A/ja
Priority to CA002519576A priority patent/CA2519576A1/fr
Priority to EP04757792A priority patent/EP1604004A1/fr
Priority to PCT/US2004/008231 priority patent/WO2004085600A1/fr
Priority to CNA200480009616XA priority patent/CN1771319A/zh
Priority to AU2004223907A priority patent/AU2004223907A1/en
Publication of US20040186034A1 publication Critical patent/US20040186034A1/en
Priority to US11/366,150 priority patent/US7642226B2/en
Publication of US7022656B2 publication Critical patent/US7022656B2/en
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Assigned to MONOSOL, LLC, CELANESE INTERNATIONAL CORPORATION reassignment MONOSOL, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MONOSOL, LLC
Assigned to DEUTSCHE BANK AG, NEW YORK BRANCH, AS COLLATERAL AGENT reassignment DEUTSCHE BANK AG, NEW YORK BRANCH, AS COLLATERAL AGENT ASSIGNMENT OF SECURITY INTEREST IN CERTAIN PATENTS Assignors: CELANESE INTERNATIONAL CORPORATION
Priority to AU2009201504A priority patent/AU2009201504A1/en
Assigned to CELANESE INTERNATIONAL CORP. reassignment CELANESE INTERNATIONAL CORP. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: DEUTSCHE BANK AG
Assigned to SEKISUI SPECIALTY CHEMICALS AMERICA, LLC reassignment SEKISUI SPECIALTY CHEMICALS AMERICA, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CELANESE EMULSIONS GMBH, CELANESE INTERNATIONAL CORPORATION, Celanese Ltd.
Assigned to CELANESE INTERNATIONAL CORPORATION reassignment CELANESE INTERNATIONAL CORPORATION RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: DEUTSCHE BANK AG, NEW YORK BRANCH
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
    • C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
    • C11D17/042—Water soluble or water disintegrable containers or substrates containing cleaning compositions or additives for cleaning compositions
    • C11D17/043—Liquid or thixotropic (gel) compositions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1334—Nonself-supporting tubular film or bag [e.g., pouch, envelope, packet, etc.]

Definitions

  • the present invention relates generally to polyvinyl alcohol copolymer film for packaging liquid products, such as, for example, laundry detergent. More specifically, the present invention relates to polyvinyl alcohol copolymer film wherein the copolymer has structural features which provide an improved film shelf-life.
  • Polyvinyl alcohol is a synthetic resin generally prepared by the alcoholysis, usually termed hydrolysis or saponification, of polyvinyl acetate.
  • Fully hydrolyzed PVOH where virtually all the acetate groups have been converted to alcohol groups, is a strongly hydrogen-bonded, highly crystalline polymer which dissolves only in hot water—greater than about 140° F. (60° C.). If a sufficient number of acetate groups are allowed to remain after the hydrolysis of polyvinyl acetate, the PVOH polymer then being known as partially hydrolyzed, it is more weakly hydrogen-bonded and less crystalline and is soluble in cold water—less than about 50° F. (10° C.). Both fully and partially hydrolyzed PVOH types are commonly referred to as PVOH homopolymers although the partially hydrolyzed type is technically a vinyl alcohol-vinyl acetate copolymer.
  • PVOH copolymer is generally used to describe polymers that are derived by the hydrolysis of a copolymer of a vinyl ester, typically vinyl acetate, and another monomer. PVOH copolymers can be tailored to desired film characteristics by varying the kind and quantity of copolymerized monomers. Examples of copolymerizations are those of vinyl acetate with a carboxylic acid or with an ester of a carboxylic acid. Again, if the hydrolysis of acetate groups in these copolymers is only partial, then the resulting polymer could be described as a PVOH terpolymer—having vinyl acetate, vinyl alcohol, and carboxylate groups—although it is commonly referred to as a copolymer.
  • copolymers examples include those prepared by the hydrolysis (base catalyzed alcoholysis) of copolymers of vinyl acetate and carboxylic acid vinyl monomers, and copolymers of vinyl acetate and esters of carboxylic acid vinyl monomers. If sufficient base is present such that the acid groups (including those resulting from ester hydrolysis) are neutralized to form carboxylate salt groups i.e., ionomer groups, the cold water-solubility of these PVOH copolymers, and hence films fabricated from them, is very rapid.
  • Examples of carboxylate-containing PVOH copolymers derived from monocarboxylic acid vinyl monomers and their esters are those prepared by the hydrolysis of a vinyl acetate-acrylic acid copolymer, a vinyl acetate-crotonic acid copolymer, a vinyl acetate-methyl acrylate copolymer, a vinyl acetate-methacrylic acid copolymer, and a vinyl acetate-methyl methacrylate copolymer, all of which have excellent cold water-solubility.
  • packaging films based on PVOH copolymers having carboxylate groups are generally considered in the art to be the most rapidly cold water-soluble films.
  • the commercial film is based on a carboxylate-containing PVOH copolymer where the carboxylate units, if converted to carboxylic acid groups, are readily able to form stable lactones by cyclizing with adjacent hydroxyl groups.
  • the chemical incompatibility derives from the acid-base equilibria that exist in the liquid laundry detergent formulations and are usually in the form of amine-fatty acid equilibria and/or amine-anionic surfactant acid equilibria.
  • a water-soluble copolymer film is disclosed for use in making pouches to contain a liquid material, such as a liquid laundry detergent, wherein the film solubility is not significantly affected adversely by the detergent.
  • a liquid material such as a liquid laundry detergent
  • Such film produces pouches having a greater storage shelf-life over prior art water-soluble film.
  • the present water-soluble film comprises vinyl acetate copolymerized with itaconic acid as a second monomer to produce, after hydrolysis, a polyvinyl alcohol copolymer with a degree of hydrolysis, expressed as a percentage of vinyl acetate units converted to vinyl alcohol units, from about 98% to about 100%.
  • the second monomer may be selected from the group of monomers consisting of monocarboxylic acid vinyl monomers, their esters and anhydrides, dicarboxylic monomers having a polymerizable double bond, their esters and anhydrides, and vinyl sulfonic acid monomers and their alkali metal salts.
  • the degree of hydrolysis for these copolymer embodiments varies.
  • the second monomer is one of either monocarboxylic acid vinyl monomers, their esters and anhydrides, dicarboxylic monomers having a polymerizable double bond, or their esters and anhydrides
  • the monomer be specifically selected from the group consisting of vinyl acetic acid, maleic acid, monomethyl maleate, dimethyl maleate, maleic anhydride, itaconic acid, monomethyl itaconate, dimethyl itaconate, and itaconic anhydride.
  • the second monomer is itaconic acid.
  • the second monomer is a vinyl sulfonic acid monomer or its alkali metal salts.
  • the second monomer is selected from the group of sulfonic acid monomers and their alkali metal salts consisting of vinyl sulfonic acid, allyl sulfonic acid, ethylene sulfonic acid, 2-acrylamido-1-methylpropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-methylacrylamido-2-methylpropanesulfonic acid, and 2-sulfoethyl acrylate.
  • the second monomer for these embodiments is 2-acrylamido-2-methylpropanesulfonic acid.
  • the present invention is a water-soluble copolymer film comprising vinyl acetate copolymerized with a second monomer to produce a polyvinyl alcohol copolymer having certain structural features which serve to improve the shelf life of the film, and wherein the second monomer is selected from the group consisting of monomers having carboxylate functionality or sulfonate functionality.
  • It is another aspect of the disclosed invention to produce a liquid product packet comprising a water-soluble film comprised of a polyvinyl alcohol copolymer wherein a comonomer of the film copolymer is selected from the group consisting of monocarboxylic acid vinyl monomers, their esters and anhydrides, dicarboxylic monomers having a polymerizable double bond, their esters and anhydrides or vinyl sulfonic acid monomers and their alkali metal salts.
  • the present embodiment includes a quantity of a liquid product enclosed within the water-soluble film packet.
  • FIG. 1 is a perspective view of a test apparatus used to determine the water disintegration and dissolution times of film samples
  • FIG. 2 is a perspective view of the test apparatus and test set-up illustrating the procedure for determining the water-solubility of film samples
  • FIG. 3 is a top view of the test set-up of FIG. 2 .
  • specific monomers within three general chemical classes are selected for copolymerization with vinyl acetate such that the base-catalyzed alcoholysis products of these copolymers, which are used in the formulation of the water-soluble film, retain excellent solubility performance in the presence of hydrogen ions.
  • the copolymers used in the formulation of the water-soluble films have one of either 1) carboxylate functionality or 2) sulfonate functionality.
  • Specific monocarboxylic acid vinyl monomers for example, structure (a) shown below
  • specific dicarboxylic monomers for example, structure (b) shown below
  • vinyl acetate Specific monocarboxylic acid vinyl monomers (for example, structure (a) shown below) and their esters and anhydrides, and specific dicarboxylic monomers (for example, structure (b) shown below) having a polymerizable double bond and their esters and anhydrides are selected for copolymerization with vinyl acetate.
  • the base-catalyzed alcoholysis products of these copolymers which are used in the formulation of the water-soluble film, retain carboxylate functionality in the presence of hydrogen ions because of the low steric stability, and therefore non-formation, of six-membered (delta, ⁇ ) lactone rings.
  • the selected monomers are vinyl acetic acid, maleic acid, monomethyl maleate, dimethyl maleate, maleic anhydride, itaconic acid, monomethyl itaconate, dimethyl itaconate and itaconic anhydride.
  • structures (c) and (d) are provided to show the sterically favored ⁇ -lactone and the non-favored ⁇ -lactone, respectively, as they would form on the polyvinyl alcohol polymer backbone:
  • a carboxylate-containing PVOH copolymer based on the copolymerization of, for example, acrylic acid with vinyl acetate would have its carboxylate unit directly attached to the polymer backbone and therefore, when in the acid form, able to form a stable five-membered ⁇ -lactone (structure (c) above) by cyclizing with an adjacent hydroxyl group.
  • a copolymer derived from vinyl acetic acid would have a methylene group between the polymer backbone and the carboxylate unit; in this case, only a six-membered ⁇ -lactone (structure (d) above) could form and this is not a sterically favorable entity.
  • one of the carboxylate groups can ultimately form a ⁇ -lactone but the other can only form a ⁇ -lactone; the latter therefore remains intact and film solubility is preserved.
  • the preferred monomer for copolymerization with vinyl acetate from the group of monomers providing carboxylate functionality is itaconic acid.
  • the preferred water-soluble film is therefore based on a vinyl alcohol-co-itaconic acid (sodium salt) copolymer.
  • the vinyl acetate-co-itaconic acid copolymer is prepared under nitrogen, and in methanol as solvent, using 2,2′-azobis(isobutyronitrile) (AIBN) as initiator. Alcoholysis of this copolymer is carried out in methanolic sodium hydroxide and the recovered vinyl alcohol-co-itaconic acid (sodium salt) copolymer is ground, washed to remove residual sodium acetate, and dried. These reactions are known in the art and have been reported, for example, by Moritani et. al (Polymer Preprints, Japan, 31, 126 (1982)).
  • the preferred degree of polymerization of the vinyl alcohol-co-itaconic acid (sodium salt) copolymer is such that the viscosity of a 4% aqueous solution at 20° C. is within a range of from about 5 to about 45 MPa.s (cps), including all ranges and combination of ranges which are a subset thereof. More preferred is a range of 11–30 MPa.s and especially preferred is a range of 15–25 MPa.s.
  • the preferred level of incorporation of itaconic acid comonomer in the vinyl alcohol-co-itaconic acid (sodium salt) copolymer is within the range of from about 1.5 to about 11 mole %, including all ranges and combination of ranges which are a subset thereof. More preferred is a range of 2.5–8.5 mole % and especially preferred is a range of 4–6 mole %.
  • the preferred degree of hydrolysis of the vinyl alcohol-co-itaconic acid (sodium salt) copolymer of the present invention is within the range of from about 98 to 100%.
  • vinyl sulfonic acid monomers and their alkali metal salts are selected for copolymerization with vinyl acetate; the base-catalyzed alcoholysis products of these copolymers, which are used in the formulation of the water-soluble film, are vinyl alcohol-sulfonate salt copolymers which are rapidly soluble.
  • the sulfonate group may revert to sulfonic acid in the presence of hydrogen ions but the sulfonic acid group still provides for excellent cold water solubility of the film.
  • the selected sulfonic acid monomers include vinyl sulfonic acid, allyl sulfonic acid, ethylene sulfonic acid, 2-acrylamido-1-methylpropanesulfonic acid, 2-acrylamido-2-methylpropanesufonic acid, 2-methacrylamido-2-methylpropanesulfonic acid and 2-sulfoethyl acrylate.
  • the preferred monomer for copolymerization with vinyl acetate from the group of monomers providing sulphonate functionality is the sodium salt of 2-acrylamido-2-methylpropanesulfonic acid (AMPS) and the preferred copolymer for incorporation into the water-soluble film is therefore a vinyl alcohol-co-AMPS (sodium salt) copolymer.
  • AMPS 2-acrylamido-2-methylpropanesulfonic acid
  • the vinyl acetate-co-AMPS copolymer is prepared under nitrogen in methanol as solvent, using 2,2′-azobis(isobutyronitrile) (AIBN) as initiator. Alcoholysis of this copolymer is carried out in methanolic sodium hydroxide and the recovered vinyl alcohol-co-AMPS (sodium salt) copolymer is ground, washed to remove residual sodium acetate, and dried. These reactions are known in the art and have been reported, for example, by Moritani and Yamauchi (Polymer, 39 (3), 553–557 (1998)).
  • the preferred degree of polymerization of the vinyl alcohol-co-AMPS (sodium salt) copolymer is such that the viscosity of a 4% aqueous solution at 20° C. is in the range of from about 3 to about 18 MPa.s (cps), including all ranges and combination of ranges which are a subset thereof. More preferred is a range of from about 4 to about 12 MPa.s.
  • the preferred level of incorporation of AMPS comonomer in the vinyl alcohol-co-AMPS (sodium salt) copolymer is in the range of from about 1 to about 8 mole %, including all ranges and combination of ranges which are a subset thereof. More preferred is a range of from about 2.5 to about 5 mole %.
  • the preferred degree of hydrolysis of the vinyl alcohol-co-AMPS (sodium salt) copolymer is in the range of from about 90 to about 99%. More preferred is a range of from about 94 to about 98%.
  • the preferred amount of the copolymer with carboxylate or sulfonate functionality in the water-soluble film of the present invention is in the range of from about 40% to about 90% by weight, including all ranges and combination of ranges therein. More preferably the amount of these copolymers is in the range of from about 60% to about 80% by weight.
  • the water-soluble film of the present invention in addition to the copolymer with carboxylate or sulfonate functionality, may contain plasticizers, lubricants, release agents, fillers, extenders, antiblocking agents, detackifying agents, antifoams and other functional ingredients.
  • plasticizers include, but are not limited to, glycerin, diglycerin, sorbitol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, polyethylene glycols up to 400 MW, neopentyl glycol, trimethylolpropane, polyether polyols and ethanolamines.
  • Preferred plasticizers are glycerin, triethyleneglycol, propylene glycol and trimethylolpropane.
  • the preferred amount of plasticizer incorporated in the water-soluble film of the present invention is in the range of from about 5% to about 30% by weight, more preferably in the range of from about 12% to about 20% by weight.
  • Suitable surfactants may include the nonionic, cationic, anionic and zwitterionic classes.
  • the surfactants will be of the nonionic, cationic or zwitterionic classes or combinations of these.
  • Suitable surfactants include, but are not limited to, polyoxyethylenated polyoxypropylene glycols, alcohol ethoxylates, alkylphenol ethoxylates, tertiary acetylenic glycols and alkanolamides (nonionics), polyoxyethylenated amines, quaternary ammonium salts and quaternized polyoxyethylenated amines (cationics), and amine oxides, N-alkylbetaines and sulfobetaines (zwitterionics).
  • Preferred surfactants are alcohol ethoxylates, quaternary ammonium salts and amine oxides.
  • the preferred amount of surfactant in the water-soluble film of the present invention is in the range of from about 0.01% to about 1% by weight, more preferably from about 0.1% to about 0.6% by weight.
  • Suitable lubricants/release agents include, but are not limited to, fatty acids and their salts, fatty alcohols, fatty esters, fatty amines, fatty amine acetates and fatty amides.
  • Preferred lubricants/release agents are fatty acids, fatty acid salts, and fatty amine acetates.
  • the preferred amount of lubricant/release agent in the water-soluble film of the present invention is within the range of from about 0.02% to about 1.5% by weight, more preferably from about 0.04% to about 0.15% by weight.
  • Suitable fillers/extenders/antiblocking agents/detackifying agents include, but are not limited to, starches, modified starches, crosslinked polyvinylpyrrolidone, crosslinked cellulose, microcrystalline cellulose, silica, metallic oxides, calcium carbonate, talc and mica. Preferred materials are starches, modified starches and silica.
  • the preferred amount of filler/extender/antiblocking agent/detackifying agent in the water-soluble film of the present invention is in the range of from about 0.1% to about 25% by weight, more preferably from about 1% to about 15% by weight. In the absence of starch, the preferred range for a suitable filler/extender/aniblocking agent/detackifying agent is from about 1% to about 5% by weight.
  • Suitable antifoams include, but are not limited to, those based on polydimethylsiloxanes and hydrocarbon blends.
  • the preferred amount of antifoam in the water-soluble film of the present invention is in the range of from about 0.001% to about 0.5%, and more preferably from about 0.01% to about 0.1% by weight.
  • the desired film thickness is within the range of from about 5 to about 200 ⁇ m, preferably within the range of from about 20 to about 100 ⁇ m, and most preferably from about 40 to about 85 ⁇ m.
  • the data below represents comparative chemical compatibility testing of two PVOH copolymer films.
  • the first film is a vinyl alcohol-co-itaconic acid (sodium salt) copolymer-based film representing the invention of the present application (Film 1), while the second film is based on a hydrolyzed vinyl acetate-methyl acrylate copolymer (Film 2).
  • the two films were cast with similar additives as detailed above to create workable film samples having the characteristics detailed in Table 1. Film thicknesses measured approximately 76 microns.
  • Pouches having dimensions of approximately 7.5 cm ⁇ 7.5 cm (about 3 in. ⁇ 3 in.) and open on one side were prepared using conventional heat-sealing equipment.
  • the test method is used to determine the time required for a water-soluble film to break apart (disintegrate) and its subsequent dissolution time under controlled conditions of water temperature and agitation. Before film solubility testing, the pouch was opened, the liquid detergent was discarded, and the film was cleaned by wiping with an absorbent paper towel.
  • test procedure is disclosed with reference to appended FIGS. 1–3 .
  • the results should include the following:
  • Exposed film disintegration time (in seconds) and the time for complete dissolution (in seconds) were obtained (e.g., 27 s/50 s), with the results of the five week testing being reported in Table 2 below.
  • Solubility time increases for Film 1 are 30% for disintegration—from 27 seconds to 35 seconds—and 50% for complete dissolution—from 50 seconds to 75 seconds—reflecting the conversion of one of the carboxylate groups deriving from the itaconate moeity to a ⁇ -lactone while the other carboxylate group remains unaffected by hydrogen ions in the detergent formulation.
  • the solubility time increases for Film 2 are 188% for disintegration—from 33 seconds to 95 seconds—and 333% for complete dissolution—from 58 seconds to 251 seconds—reflecting a substantial conversion of the carboxylate groups present in the copolymer of Film 2, all of which are capable of forming ⁇ -lactones.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Wrappers (AREA)
  • Detergent Compositions (AREA)
  • Bag Frames (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
US10/392,030 2003-03-19 2003-03-19 Water-soluble copolymer film packet Expired - Lifetime US7022656B2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US10/392,030 US7022656B2 (en) 2003-03-19 2003-03-19 Water-soluble copolymer film packet
US10/723,647 US6787512B1 (en) 2003-03-19 2003-11-26 Water-soluble copolymer film packet
JP2006507299A JP2006521449A (ja) 2003-03-19 2004-03-18 液体製品包装用の、改良された品質保持期間を有するポリビニルアルコールコポリマーフィルム
CA002519576A CA2519576A1 (fr) 2003-03-19 2004-03-18 Film en copolymere d'alcool polyvinylique servant d'emballage pour produits liquides et possedant une plus grande duree de conservation
EP04757792A EP1604004A1 (fr) 2003-03-19 2004-03-18 Film en copolymere d'alcool polyvinylique servant d'emballage pour produits liquides et possedant une plus grande duree de conservation
PCT/US2004/008231 WO2004085600A1 (fr) 2003-03-19 2004-03-18 Film en copolymere d'alcool polyvinylique servant d'emballage pour produits liquides et possedant une plus grande duree de conservation
CNA200480009616XA CN1771319A (zh) 2003-03-19 2004-03-18 用于包装液体产品和具有改进存放期的聚乙烯醇共聚物膜
AU2004223907A AU2004223907A1 (en) 2003-03-19 2004-03-18 Polyvinyl alcohol copolymer film for packaging liquid products and having an improved shelf-life
US11/366,150 US7642226B2 (en) 2003-03-19 2006-03-02 Polyvinyl alcohol copolymer film for packaging liquid products and having an improved shelf-life
AU2009201504A AU2009201504A1 (en) 2003-03-19 2009-04-17 Polyvinyl alcohol copolymer film for packaging liquid products and having an improved shelf life

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Application Number Priority Date Filing Date Title
US10/392,030 US7022656B2 (en) 2003-03-19 2003-03-19 Water-soluble copolymer film packet

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US10/723,647 Continuation US6787512B1 (en) 2003-03-19 2003-11-26 Water-soluble copolymer film packet
US11/366,150 Continuation US7642226B2 (en) 2003-03-19 2006-03-02 Polyvinyl alcohol copolymer film for packaging liquid products and having an improved shelf-life

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US20040186034A1 US20040186034A1 (en) 2004-09-23
US7022656B2 true US7022656B2 (en) 2006-04-04

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US10/392,030 Expired - Lifetime US7022656B2 (en) 2003-03-19 2003-03-19 Water-soluble copolymer film packet
US10/723,647 Expired - Lifetime US6787512B1 (en) 2003-03-19 2003-11-26 Water-soluble copolymer film packet
US11/366,150 Expired - Lifetime US7642226B2 (en) 2003-03-19 2006-03-02 Polyvinyl alcohol copolymer film for packaging liquid products and having an improved shelf-life

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US10/723,647 Expired - Lifetime US6787512B1 (en) 2003-03-19 2003-11-26 Water-soluble copolymer film packet
US11/366,150 Expired - Lifetime US7642226B2 (en) 2003-03-19 2006-03-02 Polyvinyl alcohol copolymer film for packaging liquid products and having an improved shelf-life

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US (3) US7022656B2 (fr)
EP (1) EP1604004A1 (fr)
JP (1) JP2006521449A (fr)
CN (1) CN1771319A (fr)
AU (2) AU2004223907A1 (fr)
CA (1) CA2519576A1 (fr)
WO (1) WO2004085600A1 (fr)

Cited By (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060035042A1 (en) * 2004-08-10 2006-02-16 Morken Peter A Copolymers of vinyl alcohol and itaconic acid and uses thereof
US20060063691A1 (en) * 2004-09-17 2006-03-23 The Procter & Gamble Company Water-soluble, liquid-containing pouch
WO2007111888A1 (fr) 2006-03-22 2007-10-04 The Procter & Gamble Company Composition de traitement liquide en doses unitaires
US20070254017A1 (en) * 2006-05-01 2007-11-01 Verrall Andrew P Halogen-resistant composition
US20080171825A1 (en) * 2003-12-15 2008-07-17 Elliott Echt Copolymers of Vinyl alcohol and Itaconic acid for use in paper coatings
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US20060148668A1 (en) 2006-07-06
US7642226B2 (en) 2010-01-05
AU2009201504A1 (en) 2009-05-14
CN1771319A (zh) 2006-05-10
EP1604004A1 (fr) 2005-12-14
US6787512B1 (en) 2004-09-07
CA2519576A1 (fr) 2004-10-07
US20040186034A1 (en) 2004-09-23

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